[(2R,3S,6R)-6-(2,2-dimethylpropanoyloxy)-2-pentyl-3,6-dihydro-2H-pyran-3-yl] pyridine-2-carboxylate | 1171014-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [(2R,3S,6R)-6-(2,2-dimethylpropanoyloxy)-2-pentyl-3,6-dihydro-2H-pyran-3-yl] pyridine-2-carboxylate
• CAS: 1171014-22-4
• 化学式: C₂₁H₂₉NO₅
• 分子量: 375.465
• InChiKey: VMAFPCJBZWVMRQ-FGTMMUONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3S,6R)-6-(2,2-dimethylpropanoyloxy)-2-pentyl-3,6-dihydro-2H-pyran-3-yl] pyridine-2-carboxylate 、 以 四氢呋喃 为溶剂， 反应 1.0h， 以92%的产率得到[(2R,3S,6R)-6-pentyl-3-propan-2-yl-3,6-dihydro-2H-pyran-2-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Allylic substitution on the pyran ring

  摘要：

  Allylic substitution of pyrans 10 and 15 possessing the picolinoxy leaving group with several alkyl and aryl copper reagents derived from RMgBr and CUBr center dot Me2S was studied. First, reaction of 10 with three copper reagents derived from EtMgBr (2 equiv) and different equivalents of CuBr center dot Me2S (2, 1, and 0.5 equiv, respectively) was examined in THF at -20 degrees C for 1 h to afford anti S(N)2' product 16a in high yields in all cases. Under these reaction conditions Me, i-Pr, Ph, o-MeC6H4, and o-MeOC6H4 were installed on the pyran ring of 10 successfully. Similar results were also obtained with pyran 15. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.018
• 作为产物：
  描述：

  2-吡啶甲酸 、 (2R,5S,6R)-5-hydroxy-6-pentyl-5,6-dihydro-2H-pyran-2-yl pivalate 在 N,N'-二环己基碳二亚胺 作用下， 以96%的产率得到[(2R,3S,6R)-6-(2,2-dimethylpropanoyloxy)-2-pentyl-3,6-dihydro-2H-pyran-3-yl] pyridine-2-carboxylate
  参考文献：
  名称：

  Allylic substitution on the pyran ring

  摘要：

  Allylic substitution of pyrans 10 and 15 possessing the picolinoxy leaving group with several alkyl and aryl copper reagents derived from RMgBr and CUBr center dot Me2S was studied. First, reaction of 10 with three copper reagents derived from EtMgBr (2 equiv) and different equivalents of CuBr center dot Me2S (2, 1, and 0.5 equiv, respectively) was examined in THF at -20 degrees C for 1 h to afford anti S(N)2' product 16a in high yields in all cases. Under these reaction conditions Me, i-Pr, Ph, o-MeC6H4, and o-MeOC6H4 were installed on the pyran ring of 10 successfully. Similar results were also obtained with pyran 15. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.018

文献信息

• Allylic substitution on the pyran ring
  作者：Tomonori Hyodo、Yuji Katayama、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2009.03.018

  日期：2009.7

  Allylic substitution of pyrans 10 and 15 possessing the picolinoxy leaving group with several alkyl and aryl copper reagents derived from RMgBr and CUBr center dot Me2S was studied. First, reaction of 10 with three copper reagents derived from EtMgBr (2 equiv) and different equivalents of CuBr center dot Me2S (2, 1, and 0.5 equiv, respectively) was examined in THF at -20 degrees C for 1 h to afford anti S(N)2' product 16a in high yields in all cases. Under these reaction conditions Me, i-Pr, Ph, o-MeC6H4, and o-MeOC6H4 were installed on the pyran ring of 10 successfully. Similar results were also obtained with pyran 15. (C) 2009 Elsevier Ltd. All rights reserved.